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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-05-22 19:11:00 UTC

Update Date

2022-03-07 02:49:30 UTC

HMDB ID

HMDB0006245

Secondary Accession Numbers

HMDB0011642
HMDB06245
HMDB11642

Metabolite Identification

Common Name

18-Hydroxyarachidonic acid

Description

(18R)-Hydroxyarachidonate is a substrate for CYP4F8 or leukotriene-B4 20-monooxygenase (EC 1.14.13.30). This enzyme hydroxylates arachdonic acid (20:4n-6) to (18R)-hydroxyarachidonate in the endoplasmic reticulum. This reaction is irreversible. CYP4F8 is a member of the cytochrome P450 superfamily of enzymes. The cytochrome P450 proteins are monooxygenases which catalyze many reactions involved in drug metabolism and synthesis of cholesterol, steroids and other lipids. This protein localizes to the endoplasmic reticulum and functions as a 19-hydroxylase of prostaglandins in seminal vesicles. In particular, CYP4F8 catalyzes the 2-hydroxylation of PGH1 and PGH2, which will lead to biosynthesis of the two main PGs of human seminal fluid, (19R)-hydroxy-PGE1 and (19R)-hydroxy-PGE2 (PMID: 10791960 ). 18-Hydroxyarachidonic acid is an intermediate in eicosanoid metabolism.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0006245
     RDKit          3D
18-Hydroxyarachidonic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
   -6.3448    2.2853    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6702    1.5742    2.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6336    0.1098    2.0504 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9536   -0.3979    1.9257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5825   -0.6613    1.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1722   -0.5494    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5603    0.7234   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3291    0.7922   -0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269   -0.3521   -1.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439   -0.0965   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9732    0.0170   -0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3355   -0.0859   -2.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538   -1.1396   -2.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7872   -2.0558   -1.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566   -2.3215   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7806   -2.1880    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9812   -1.7723    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5592   -1.3095   -0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0823    0.0922   -0.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1462    1.1901   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4986    1.2725    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341    0.5869    1.7541 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    2.2396    0.9016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3819    2.6363    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7773    3.2039    0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4900    1.6071    0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6470    2.0140    2.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2431    1.9025    3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4903   -0.1833    3.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0664   -0.8141    1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6494   -0.5603    2.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8339   -1.7683    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5538   -1.4262   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0916   -0.7305   -0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1139    1.6867   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.8091   -1.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1720   -0.5186   -2.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8634   -1.3466   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074    0.0031    0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8158    0.2320    0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    0.9485   -2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4387   -0.1167   -2.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141   -1.1358   -3.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4257   -2.7955   -2.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4814   -3.5191   -0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821   -2.0554    0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -2.4880    1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7223   -1.7848    1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0416   -1.4739   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5316   -1.9537   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9004    0.0739   -0.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6664    0.2883   -1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292    2.1772   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3822    1.2559   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6061    2.8508    1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  1
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END


  Mrv0541 02231220352D          

 23 22  0  0  1  0            999 V2000
   12.4596   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8721   -3.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6971   -3.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1096   -4.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9346   -4.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3471   -4.9799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9346   -5.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3471   -6.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9346   -7.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1096   -7.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6971   -7.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8721   -7.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4596   -7.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6346   -7.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2221   -6.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6346   -5.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2221   -4.9799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6346   -4.2654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2221   -3.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3971   -3.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6346   -2.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8721   -2.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4596   -4.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 21  2  0  0  0  0
  1 22  1  0  0  0  0
 18 23  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0006245

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@@H](O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-/t19-/m1/s1

> <INCHI_KEY>
PPCHNRUZQWLEMF-LFFPGIGVSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.4663

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.21322145890687

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z,18R)-18-hydroxyicosa-5,8,11,14-tetraenoic acid

> <ALOGPS_LOGP>
5.81

> <JCHEM_LOGP>
5.200452284

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.365538512332495

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819772150477412

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3267137646609193

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.62349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18-hydroxy-arachidonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006245
     RDKit          3D
18-Hydroxyarachidonic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
   -6.3448    2.2853    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6702    1.5742    2.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6336    0.1098    2.0504 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9536   -0.3979    1.9257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5825   -0.6613    1.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1722   -0.5494    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5603    0.7234   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3291    0.7922   -0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269   -0.3521   -1.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439   -0.0965   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9732    0.0170   -0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3355   -0.0859   -2.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538   -1.1396   -2.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7872   -2.0558   -1.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566   -2.3215   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7806   -2.1880    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9812   -1.7723    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5592   -1.3095   -0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0823    0.0922   -0.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1462    1.1901   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4986    1.2725    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341    0.5869    1.7541 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    2.2396    0.9016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3819    2.6363    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7773    3.2039    0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4900    1.6071    0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6470    2.0140    2.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2431    1.9025    3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4903   -0.1833    3.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0664   -0.8141    1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6494   -0.5603    2.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8339   -1.7683    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5538   -1.4262   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0916   -0.7305   -0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1139    1.6867   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.8091   -1.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1720   -0.5186   -2.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8634   -1.3466   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074    0.0031    0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8158    0.2320    0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    0.9485   -2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4387   -0.1167   -2.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141   -1.1358   -3.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4257   -2.7955   -2.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4814   -3.5191   -0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821   -2.0554    0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -2.4880    1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7223   -1.7848    1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0416   -1.4739   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5316   -1.9537   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9004    0.0739   -0.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6664    0.2883   -1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292    2.1772   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3822    1.2559   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6061    2.8508    1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  1
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      23.258  -5.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.028  -6.628   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.568  -6.628   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.338  -7.962   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.878  -7.962   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.648  -9.296   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.878 -10.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.648 -11.963   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.878 -13.297   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.338 -13.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.568 -14.631   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.028 -14.631   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.258 -13.297   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.718 -13.297   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.948 -11.963   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.718 -10.629   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.948  -9.296   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.718  -7.962   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.948  -6.628   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.408  -6.628   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      21.718  -5.295   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      24.028  -3.961   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      23.258  -7.962   0.000  0.00  0.00           O+0
CONECT    1    2   21   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0006245
HETATM    1  C1  UNL     1      -6.345   2.285   0.978  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.670   1.574   2.131  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.634   0.110   2.050  1.00  0.00           C  
HETATM    4  O1  UNL     1      -6.954  -0.398   1.926  1.00  0.00           O  
HETATM    5  C4  UNL     1      -4.582  -0.661   1.433  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.172  -0.549   0.019  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.560   0.723  -0.366  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.329   0.792  -0.822  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.427  -0.352  -1.003  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.244  -0.096  -0.146  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.973   0.017  -0.608  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.335  -0.086  -2.003  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.254  -1.140  -2.437  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.787  -2.056  -1.694  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.657  -2.322  -0.302  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.781  -2.188   0.606  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.981  -1.772   0.382  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.559  -1.310  -0.847  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.082   0.092  -0.806  1.00  0.00           C  
HETATM   20  C19 UNL     1       5.146   1.190  -0.540  1.00  0.00           C  
HETATM   21  C20 UNL     1       4.499   1.273   0.758  1.00  0.00           C  
HETATM   22  O2  UNL     1       4.734   0.587   1.754  1.00  0.00           O  
HETATM   23  O3  UNL     1       3.492   2.240   0.902  1.00  0.00           O  
HETATM   24  H1  UNL     1      -7.382   2.636   1.246  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.777   3.204   0.720  1.00  0.00           H  
HETATM   26  H3  UNL     1      -6.490   1.607   0.111  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.647   2.014   2.321  1.00  0.00           H  
HETATM   28  H5  UNL     1      -6.243   1.903   3.052  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.490  -0.183   3.220  1.00  0.00           H  
HETATM   30  H7  UNL     1      -7.066  -0.814   1.056  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.649  -0.560   2.084  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.834  -1.768   1.607  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.554  -1.426  -0.226  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.092  -0.731  -0.659  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.114   1.687  -0.301  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.951   1.809  -1.090  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.172  -0.519  -2.069  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.863  -1.347  -0.699  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.407   0.003   0.952  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.816   0.232   0.123  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.816   0.948  -2.321  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.439  -0.117  -2.687  1.00  0.00           H  
HETATM   43  H20 UNL     1       2.514  -1.136  -3.543  1.00  0.00           H  
HETATM   44  H21 UNL     1       3.426  -2.796  -2.300  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.481  -3.519  -0.254  1.00  0.00           H  
HETATM   46  H23 UNL     1       1.682  -2.055   0.192  1.00  0.00           H  
HETATM   47  H24 UNL     1       3.616  -2.488   1.699  1.00  0.00           H  
HETATM   48  H25 UNL     1       5.722  -1.785   1.251  1.00  0.00           H  
HETATM   49  H26 UNL     1       5.042  -1.474  -1.795  1.00  0.00           H  
HETATM   50  H27 UNL     1       6.532  -1.954  -0.972  1.00  0.00           H  
HETATM   51  H28 UNL     1       6.900   0.074  -0.006  1.00  0.00           H  
HETATM   52  H29 UNL     1       6.666   0.288  -1.748  1.00  0.00           H  
HETATM   53  H30 UNL     1       5.729   2.177  -0.650  1.00  0.00           H  
HETATM   54  H31 UNL     1       4.382   1.256  -1.384  1.00  0.00           H  
HETATM   55  H32 UNL     1       3.606   2.851   1.708  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    5   29
CONECT    4   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8    8   35
CONECT    8    9   36
CONECT    9   10   37   38
CONECT   10   11   11   39
CONECT   11   12   40
CONECT   12   13   41   42
CONECT   13   14   14   43
CONECT   14   15   44
CONECT   15   16   45   46
CONECT   16   17   17   47
CONECT   17   18   48
CONECT   18   19   49   50
CONECT   19   20   51   52
CONECT   20   21   53   54
CONECT   21   22   22   23
CONECT   23   55
END

HMDB0006245
     RDKit          3D
18-Hydroxyarachidonic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
   -6.3448    2.2853    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6702    1.5742    2.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6336    0.1098    2.0504 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9536   -0.3979    1.9257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5825   -0.6613    1.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1722   -0.5494    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5603    0.7234   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3291    0.7922   -0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269   -0.3521   -1.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439   -0.0965   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9732    0.0170   -0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3355   -0.0859   -2.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538   -1.1396   -2.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7872   -2.0558   -1.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566   -2.3215   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7806   -2.1880    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9812   -1.7723    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5592   -1.3095   -0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0823    0.0922   -0.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1462    1.1901   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4986    1.2725    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341    0.5869    1.7541 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    2.2396    0.9016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3819    2.6363    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7773    3.2039    0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4900    1.6071    0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6470    2.0140    2.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2431    1.9025    3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4903   -0.1833    3.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0664   -0.8141    1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6494   -0.5603    2.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8339   -1.7683    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5538   -1.4262   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0916   -0.7305   -0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1139    1.6867   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.8091   -1.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1720   -0.5186   -2.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8634   -1.3466   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074    0.0031    0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8158    0.2320    0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    0.9485   -2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4387   -0.1167   -2.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141   -1.1358   -3.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4257   -2.7955   -2.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4814   -3.5191   -0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821   -2.0554    0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -2.4880    1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7223   -1.7848    1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0416   -1.4739   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5316   -1.9537   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9004    0.0739   -0.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6664    0.2883   -1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292    2.1772   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3822    1.2559   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6061    2.8508    1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  1
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(18R)-HETE	ChEBI
(5Z,8Z,11Z,14Z,18R)-18-Hydroxyicosatetraenoic acid	ChEBI
18(R)-Hydroxyeicosatetraenoic acid	ChEBI
Hydroxyarachidonic acid	ChEBI
(5Z,8Z,11Z,14Z,18R)-18-Hydroxyicosatetraenoate	Generator
18(R)-Hydroxyeicosatetraenoate	Generator
Hydroxyarachidonate	Generator
18-Hydroxyarachidonate	Generator
(18R)-Hydroxyarachidonate	HMDB
(18R)-Hydroxyarachidonic acid	HMDB
18-HETE	HMDB
18-Hydroxyeicosatetraenoate	HMDB
18-Hydroxyeicosatetraenoic acid	HMDB
Omega-hydroxyarachidonic acid	HMDB
W-Hydroxyarachidonic acid	HMDB
18-Hydroxy-5,8,11,14-eicosatetraenoic acid	HMDB
18-Hydroxy-arachidonate	HMDB

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(5Z,8Z,11Z,14Z,18R)-18-hydroxyicosa-5,8,11,14-tetraenoic acid

Traditional Name

18-hydroxy-arachidonic acid

CAS Registry Number

124411-81-0

SMILES

CC[C@@H](O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-/t19-/m1/s1

InChI Key

PPCHNRUZQWLEMF-LFFPGIGVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatetraenoic acids

Alternative Parents

Substituents

Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060093 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0006245)

Extracellular (HMDB: HMDB0006245)
Membrane (HMDB: HMDB0006245)

Source

Exogenous

Exogenous (HMDB: HMDB0006245)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0006245)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	5.81	ALOGPS
logP	5.2	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	101.62 m³·mol⁻¹	ChemAxon
Polarizability	38.21 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	184.518	31661259
DarkChem	[M-H]-	184.281	31661259
DeepCCS	[M+H]+	184.384	30932474
DeepCCS	[M-H]-	182.026	30932474
DeepCCS	[M-2H]-	214.912	30932474
DeepCCS	[M+Na]+	190.477	30932474
AllCCS	[M+H]+	186.8	32859911
AllCCS	[M+H-H2O]+	184.0	32859911
AllCCS	[M+NH4]+	189.5	32859911
AllCCS	[M+Na]+	190.3	32859911
AllCCS	[M-H]-	185.3	32859911
AllCCS	[M+Na-2H]-	187.1	32859911
AllCCS	[M+HCOO]-	189.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.97 minutes	32390414
Predicted by Siyang on May 30, 2022	20.5264 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.0 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3038.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	381.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	192.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	266.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	592.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1008.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	544.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1910.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	692.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1736.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	669.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	479.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	388.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	436.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
18-Hydroxyarachidonic acid	CC[C@@H](O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	4063.0	Standard polar	33892256
18-Hydroxyarachidonic acid	CC[C@@H](O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	2320.2	Standard non polar	33892256
18-Hydroxyarachidonic acid	CC[C@@H](O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	2556.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
18-Hydroxyarachidonic acid,1TMS,isomer #1	CC[C@H](CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2711.8	Semi standard non polar	33892256
18-Hydroxyarachidonic acid,1TMS,isomer #2	CC[C@@H](O)CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2587.1	Semi standard non polar	33892256
18-Hydroxyarachidonic acid,2TMS,isomer #1	CC[C@H](CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2624.6	Semi standard non polar	33892256
18-Hydroxyarachidonic acid,1TBDMS,isomer #1	CC[C@H](CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2958.8	Semi standard non polar	33892256
18-Hydroxyarachidonic acid,1TBDMS,isomer #2	CC[C@@H](O)CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2833.5	Semi standard non polar	33892256
18-Hydroxyarachidonic acid,2TBDMS,isomer #1	CC[C@H](CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3112.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 18-Hydroxyarachidonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6y-7291000000-16728ad8bd8ebb944fe2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 18-Hydroxyarachidonic acid GC-MS (2 TMS) - 70eV, Positive	splash10-009i-9436500000-0c21440f1fd79ba11984	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 18-Hydroxyarachidonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 10V, Positive-QTOF	splash10-0udi-0059000000-a75bea5dd5332be1a84f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 20V, Positive-QTOF	splash10-0udr-1292000000-ef55afde193cfcd01538	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 40V, Positive-QTOF	splash10-1000-8790000000-0eab084330a82cf88226	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 10V, Negative-QTOF	splash10-014i-0019000000-710912287685513d0e07	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 20V, Negative-QTOF	splash10-0uxr-1059000000-ad675311c547d18f97bb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 40V, Negative-QTOF	splash10-0a4l-9030000000-a7c5a41adbeb99e30dbc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 10V, Positive-QTOF	splash10-0uk9-1339000000-0392a1ab82d4e70b35db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 20V, Positive-QTOF	splash10-0fri-4953000000-34622f97ba9d1fd54e9b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 40V, Positive-QTOF	splash10-015c-9600000000-7cde68db4ec7173c6177	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 10V, Negative-QTOF	splash10-014i-0009000000-777fdb814292c66079c9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 20V, Negative-QTOF	splash10-0gb9-3059000000-c59628baf2569d14b3c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 18-Hydroxyarachidonic acid 40V, Negative-QTOF	splash10-0a4l-9020000000-d11651945eb0a6c4f27d	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Endoplasmic reticulum

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000273 +/- 0.000047 uM	Adult (>18 years old)	Both	Normal	20671299	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023857

KNApSAcK ID

Not Available

Chemspider ID

9316866

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2300206

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11141754

PDB ID

Not Available

ChEBI ID

91132

Food Biomarker Ontology

Not Available

VMH ID

18HARACHD

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Romanov, Stepan G.; Ivanov, Igor V.; Groza, Nataliya V.; Kuhn, Hartmut; Myagkova, Galina I. Total synthesis of (5Z,8Z,11Z,14Z)-18- and 19-oxoeicosa-5,8,11,14-tetraenoic acids. Tetrahedron (2002), 58(42), 8483-8487.

Material Safety Data Sheet (MSDS)

Not Available

General References

Bylund J, Hidestrand M, Ingelman-Sundberg M, Oliw EH: Identification of CYP4F8 in human seminal vesicles as a prominent 19-hydroxylase of prostaglandin endoperoxides. J Biol Chem. 2000 Jul 21;275(29):21844-9. [PubMed:10791960 ]

Enzymes

Enzyme Details

1. Leukotriene-B(4) omega-hydroxylase 1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP4F2
Uniprot ID:: P78329
Molecular weight:: 59852.825

Enzyme Details

2. Leukotriene-B(4) omega-hydroxylase 2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. This enzyme requires molecular oxygen and NADPH for the omega-hydroxylation of LTB4, a potent chemoattractant for polymorphonuclear leukocytes.
Gene Name:: CYP4F3
Uniprot ID:: Q08477
Molecular weight:: 59846.085

Showing metabocard for 18-Hydroxyarachidonic acid (HMDB0006245)

MOL for HMDB0006245 (18-Hydroxyarachidonic acid)

3D MOL for HMDB0006245 (18-Hydroxyarachidonic acid)

3D SDF for HMDB0006245 (18-Hydroxyarachidonic acid)

3D-SDF for HMDB0006245 (18-Hydroxyarachidonic acid)

PDB for HMDB0006245 (18-Hydroxyarachidonic acid)

3D PDB for HMDB0006245 (18-Hydroxyarachidonic acid)

SMILES for HMDB0006245 (18-Hydroxyarachidonic acid)

INCHI for HMDB0006245 (18-Hydroxyarachidonic acid)

Structure for HMDB0006245 (18-Hydroxyarachidonic acid)

3D Structure for HMDB0006245 (18-Hydroxyarachidonic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes